36062-04-1 Usage
Description
Tetrahydrocurcumin (THC), the active metabolite of curcumin, is gaining popularity amongst scientist due to its wide spectrum of pharmacological activities, better stability and colourless nature. Tetrahydrocurcumin has a similar structure to that of curcumin. THC lacks the α, β-unsaturated carbonyl moiety in its chemical structure. It is naturally sourced from the roots of Curcuma zedoaria, Zingiber mioga, and Zingiber officinale and has potent antioxidant activity and depigmentation of the skin. THC is being studied for the treatment of cancer and dementia. THC is also known to epigenetically ameliorate mitochondrial dysfunction in brain vasculature during Ischemic Stroke. Tetrahydrocurcumin (THC) has been used as a neuroprotective agent to study its therapeutic potential in improving mitochondrial dysfunction in the ischemic stroke mice model.
Chemical Properties
Off-white crystalline powder or Yellow Solid, soluble in methanol, ethanol, DMSO and other organic solvents, derived from turmeric bulbs.
Uses
Tetrahydrocurcumin is an antioxidant and skin-whitening ingredient. It is a major curcuminoid metabolite of curcumin that has been shown to have protective effects against diabetes and vascular dysfunction via alleviation of oxidative stress.The interest in tetrahydrocurcumin research is increasing because it is superior to curcumin in its solubility in water, chemical stability, bioavailability, and anti-oxidative activity. Curcumin metabolizes into tetrahydrocurcumin by bacterial enzyme NADPH-dependent curcumin reductase in the intestine.
Definition
ChEBI: Tetrahydrocurcumin is a beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds. It has a role as a metabolite. It is a beta-diketone, a polyphenol and a diarylheptanoid. It derives from a curcumin.
Preparation
Tetrahydrocurcumin can also be chemically synthesized from curcumin by catalytic hydrogenation using PtO2 or palladium as a catalyst.One gram (1.0 g) of curcumin was dissolved in 20 ml of acetone and placed in a 100-ml glass reactor for reduction, to which was then added 500 mg of activated Raney-nickel catalyst. Subsequently, the atmosphere of the reactor was replaced for hydrogen gas by the routine method. A rubber-made balloon filled with hydrogen gas was arranged on the upper portion of the reactor in order to keep hydrogen gas pressure constant in the reactor by supplying hydrogen gas to make up for the consumed amount of hydrogen gas. The reactor was stirred while maintained at a given temperature in a constant-temperature water bath kept at 30° C. for 2-hour reduction.After completion of the reaction, the Raney-nickel catalyst was removed from the solution by filtering, which was then evaporated and dried by concentration under reduced pressure and was dissolved again in a small amount of acetone.Subsequently, the eluate was concentrated and dried under reduced pressure to obtain 674 mg of tetrahydrocurcumin.Method for making tetrahydrocurcumin and a substance containing the antioxidative substance tetrahydrocurcumin
benefits
Tetrahydrocurcumin (ultra pure whitening element) is a natural functional whitening ingredient extracted from the roots of Ginger Curcuma longa. It has strong activity of inhibiting tyrosinase. The whitening effect is better than that of arbutin. It can effectively inhibit the generation of oxygen free radicals and remove the formed free radicals. It has obvious antioxidant, inhibits melanin, repairs freckle, anti-inflammatory activity, blocks the inflammatory process, etc. In addition, tetrahydrocurcumin has potent antioxidant activity and potential anti-aging benefits.
Biological Activity
Tetrahydrocurcumin is a metabolite of curcumin that has diverse biological activities, including antioxidant, anti-inflammatory, anti-angiogenic, and anticancer properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals in a cell-free assay with an EC50 value of 16.8 μM. Tetrahydrocurcumin (50 μM) inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 expression in RAW 264.7 cells. It also inhibits LPS-induced increases in TNF-α release when used at a concentration of 100 μM and increases in nitric oxide (NO) production and IL-6 levels in a concentration-dependent manner. Tetrahydrocurcumin reduces carrageenan-induced paw edema in rats (ED50 = 20 mg/kg). It also reduces the formation of neocapillaries and decreases microvascular density as well as VEGF, VEGF receptor 2 (VEGFR2), and hypoxia-inducible factor-1α (HIF-1α) expression in a CaSki cervical cancer nude mouse xenograft model when administered at doses of 100, 300, and 500 mg/kg.
Check Digit Verification of cas no
The CAS Registry Mumber 36062-04-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,0,6 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 36062-04:
(7*3)+(6*6)+(5*0)+(4*6)+(3*2)+(2*0)+(1*4)=91
91 % 10 = 1
So 36062-04-1 is a valid CAS Registry Number.
InChI:InChI=1/C21H24O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3
36062-04-1Relevant articles and documents
Neuroprotective effects of Tetrahydrocurcumin against glutamate-induced oxidative stress in hippocampal HT22 cells
Park, Chang-Hyun,Song, Ji Hoon,Kim, Su-Nam,Lee, Ji Hwan,Lee, Hae-Jeung,Kang, Ki Sung,Lim, Hyung-Ho
, (2020)
In the central nervous system, glutamate is a major excitable neurotransmitter responsible for many cellular functions. However, excessive levels of glutamate induce neuronal cell death via oxidative stress during acute brain injuries as well as chronic neurodegenerative diseases. The present study was conducted to examine the effect of tetrahydrocurcumin (THC), a major secondary metabolite of curcumin, and its possible mechanism against glutamate-induced cell death. We prepared THC using curcumin isolated from Curcuma longa (turmeric) and demonstrated the protective effect of THC against glutamate-induced oxidative stress in HT22 cells. THC abrogated glutamate-induced HT22 cell death and showed a strong antioxidant effect. THC also significantly reduced intracellular calcium ion increased by glutamate. Additionally, THC significantly reduced the accumulation of intracellular oxidative stress induced by glutamate. Furthermore, THC significantly diminished apoptotic cell death indicated by annexin V-positive in HT22 cells. Western blot analysis indicated that the phosphorylation of mitogen-activated protein kinases including c-Jun N-terminal kinase, extracellular signal-related kinases 1/2, and p38 by glutamate was significantly diminished by treatment with THC. In conclusion, THC is a potent neuroprotectant against glutamate-induced neuronal cell death by inhibiting the accumulation of oxidative stress and phosphorylation of mitogen-activated protein kinases.
NOVEL TETRAHYDROCURCUMIN COMPOSITIONS, METHODS OF MAKING, AND METHODS OF USING THE SAME
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, (2021/07/10)
The present invention relates to novel tetrahydrocurcumin (THCu) compositions, novel methods of manufacturing, and methods of using these compositions for therapeutic applications. The novel synthetic pathway(s) result in THCu compositions that generally lack hexahydrocurcumin (HHC), and include an improved impurity profile with reduced additional species that are generally present in hydrogenated curcumin compositions.
New insights towards 1,4-benzodiazepines from curcumin. Design, synthesis and antimicrobial activities
Hamed, Othman,Fares, Oswa,Taleeb, Shaima,Adwan, Ghaleb,Saadeh, Haythem,Jodeh, Shehdeh,Algarra, Manuel
, p. 1112 - 1123 (2020/11/09)
Background: Curcumin is a safe, versatile natural product with unlimited number of biological activities and a precursor for various heterocyclic compounds. Objective: The present study was aimed to the development of a curcumin based antimicrobial reagent with high potency against gram-positive and gram-negative bacteria. Methods: Herein we report a simple and convenient one step method for synthesizing a series of 1,4-benzodiazepines via condensation cyclization reaction between curcumin and various 1,2- phenylenediamine in refluxed ethanol. Results: A series of new 1,4-benzodiazepins were synthesized and their structures were supported by FT-IR, 1H NMR, 13C NMR, and mass spectral analysis. Synthesized 1,4-benzodiazepins were evaluated for their in vitro antimicrobial activity against gram positive (S. aureus and S. epidermidis) and gram negative (E. coli and P. aeruginosa) bacteria. They exhibited low to high potency against the tested organisms. In particular, dichlorinated 1,4-benzodiazepine 9 exhibited a remarkable potency against the gram-positive bacteria S. aureus (MIC: 3.125 μg mL?1, MBC: 12 μg mL?1). It showed a higher potency than most of the tested reference drugs. Compound 9 showed the medium activity against E. Coli. Genotoxic study revealed that, benzodiazepines 9 attacked the DNA of E. Coli strains and damaged it. The potency of compound 9, could be attributed to the multiple chlorine atoms present on the aromatic ring. Conclusion: Some of the synthesized curcumin based benzodiazepines showed excellent potency against gram positive bacteria. These benzodiazepines could be a great candidate as a future antimicrobial agent.
NOVEL TETRAHYDROCURCUMIN COMPOSITIONS, METHODS OF MAKING, AND METHODS OF USING THE SAME
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Paragraph 0023; 0029, (2020/09/19)
The present invention relates to novel tetrahydrocurcumin (THCu) compositions, novel methods of manufacturing, and methods of using these compositions for therapeutic applications. The novel synthetic pathway(s) result in THCu compositions that generally lack hexahydrocurcumin (HHC), and include an improved impurity profile with reduced additional species that are generally present in hydrogenated curcumin compositions.
